The key to "flying happiness" is to do it at a level at which you can easily afford it, at which your family/etc is happy with it (which is why many men get into GA only after they get divorced - like me) and at which the plane does mostly what you want of it. You also need to have the support personnel sorted; this involves finding maintenance / avionics people who you can trust, and that can take some time. Ownership has quite a learning curve. But it's worth it.